Ryan—On the Preparation of Amidoketones. 523 
solution of 4 gs. potassium hydrate, and about 400 c.c. alcohol, 
4 gs. of sodium nitrite were added to the well-cooled mixture, 
and acidified with good shaking by addition of 50 p. c. sulphuric 
acid. The solution was made alkaline, extracted with ether, and 
the alkaline residue let stand three days. It was acidified and 
extracted with ether. On evaporation of the solvent, an oil was 
obtained which gave colourless needles melting at 139° C. on 
standing in a vacuum desiccator over sulphuric acid. Owing to 
the method of isolation used the yield was poor. 
Analysis :— 
0:1550 g. Sbst : 0:0864 H.0, 0:3528 CO,. 
C,,Hi:NO;. Cale C 62:2, H 5-7 p.e. 
Found C 62:1, H 6:2 p.c. 
The acid dissolves easily in alcohol, scarcely in ligroin, does not 
give Liebermann’s reaction, contrary to the i-nitrosoketone gives 
a colourless alkaline solution, and a silver salt which darkens on 
standing :— 
Cy HpAg * NO;: Cale Ag: 36:0. Found 86:0 p.c. 
4. Isonitrosometarylyl acetone, CH;CO - C (OC,H,): NOH is got 
in the following manner :—Mix 28°6 gs. m-xylylacetoacetic ester 
with 20°5 gs. potash in about 4 a litre of water, and let the 
misture stand three days, with frequent shaking on the machine. 
Add 9 gs. sodium nitrite, and acidify under cooling and shaking. 
The mixture is made alkaline, and after extracting the unchanged 
ester with ether, the residue is let stand four days. lRe-acidify 
under cooling, and extract the ketone with ether. On distilling 
off the solvent, the residual oil, after some days’ standing in a 
vacuum over sulphuric acid, solidifies to bushy needles, which are 
readily soluble in alcohol, ether, and benzene. It dissolves in 
alkali with a yellow colour, and recrystallized from hot ligroin 
melted at 54-55°. Yield 4:2 gs. 
Analysis :— 
01900 g. Sbst : 0°1212 g. H,O, 0°4772 g. CO,, 
0:1298 g. Sbst : 0:0840 g. H,O, 0°3258 CO., 
0°13813 g. Sbst rll OG, IN (IGS, G7 iingon,)), 
C,, Hi; NO, Cale C 69:1, H 6:8, N 7:3 p.c. 
Found C 68°7, H 7:2, N 7:2, 
C 68:5, H 7:1 p.c. 
